Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
  • A61K8/86—Polyethers
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
  • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/60—Sugars; Derivatives thereof
  • A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/02—Preparations for cleaning the hair

Definitions

• the present invention relates to aqueous surfactant compositions having elevated viscosity which have a low foreign electrolyte content.
• the present invention relating to aqueous surfactant compositions may be used in cosmetic compositions such as, for example, shampoos, bath and shower preparations, hand-wash pastes and lotions.
• High viscosity aqueous surfactants are desirable in many cases. They are easier to handle and can be metered simply. If the composition contains a second phase (solid or liquid), the elevated viscosity also imparts higher storage stability. Moreover, higher viscosity aqueous surfactant compositions are of interest for marketing reasons, since the consumer frequently associates preparations of low viscosity with a low concentration of the active compound.
• Aqueous surfactant compositions usually contain anionic surfactants, such as, fatty alcohol ether-sulphates, fatty alcohol sulphates, fatty alcohol sulphosuccinates, alkane sulphonates or ethercarboxylic acids, as the main component, and are sometimes found in combination with betaines, ampholytic compounds or fatty acid alkanolamides, for example.
• anionic surfactants such as, fatty alcohol ether-sulphates, fatty alcohol sulphates, fatty alcohol sulphosuccinates, alkane sulphonates or ethercarboxylic acids, as the main component, and are sometimes found in combination with betaines, ampholytic compounds or fatty acid alkanolamides, for example.
• Fatty acid alkanolamides can be used as a consistency regulator, but are considered undesirable since the low content of free alkanolamine can give rise to the formation of nitrosamine as a byproduct. Nitrogen-free additives are therefore preferred, instead of the alkanolamides (compare H. Hensen et al., 2nd World Surfactant Congress, Paris 1988, Vol. II, pages 378 ff.).
• Saturated or unsaturated fatty alcohol oxethylates having low degrees of ethoxylation, preferably containing about 2.5 mol EO/mol (A. Behler et al., Seifen, Ole, Fette, Wachse 116, 60 (1990)) constitute one solution to this problem, but are also considered to be somewhat disadvantageous since they possess very high fat-dissolving power and their limited solubility in water reduces their foamability. Moreover, their effectiveness in compositions simulating those used in practice, that is to say, with realistic amount of the electrolyte is restricted to sulphate surfactants (A. Behler et al. loc. cit.).
• Thickeners for aqueous solutions which are effective irrespective of the surfactant type, belong to the group of water-soluble polymers.
• Suitable additives here are cellulose derivatives and xanthans.
• Polyethylene glycol derivatives German Patent 3,140,160
• polyol monoethers European Patent 0,303,187
• fatty acid-esterified polyoxyalkylene ethers of glycerol or propane-1,2-diol German Patent 3,239,564) or other polyhydric alcohols
• German Patent 3,843,224 alkylpolyethylene glycol ether fatty acid esters
• a thickener mixture is described in German Patent 3,843,224 which utilizes the surfactant/polymer combination in a targeted manner for surfactant compositions.
• the patent claims a mixture of a nonionic surfactant (HLB value of 4 to 11) with a polymer in a weight ratio of 10:1 to 1:10 as a thickener for other surfactant mixtures.
• Typical nonionic surfactants disclosed are oxethylates having low degrees of EO, that is to say, precisely those surfactants which, although they have a considerable thickening effect are questionable both toxicologically in respect to their tolerance by the skin and mucous membranes, and ecologically (compare P. Schobel et al., Tenside Surfactants Detergents 25.2 (1988), S. Matsumura JAOCS 67, p. 996 (1990)).
• the present invention provides for such a composition that is toxicologically, ecologically and economically superior to any previously known surfactant composition.
• the present invention has achieved this objective by providing an aqueous surfactant composition that comprises a mixture of surfactant, polymer, and optionally an electrolyte, as a thickener to a surfactant base composition.
• the present invention provides for an aqueous, cosmetic surfactant composition with an elevated viscosity comprising 4 to 30% by weight of base surfactants, and 3 to 29.5% by weight of a thickener mixture and additive, wherein the thickener mixture comprises 3 to 25% by weight of an alkyl polyglycoside, 0.005 to 2% by weight of a polymer and 0 to 2.5% by weight of a foreign electrolyte wherein the weight percentages are based on the aqueous, cosmetic surfactant composition.
• the present invention relates to the aqueous cosmetic surfactant composition described above wherein the alkyl polyglycoside is an alkyl polyglycoside having a HLB value of between 11.5 and 17.
• the present invention relates to the aqueous cosmetic surfactant composition described above that is further characterized in that the above polymer is a fatty alcohol ether or fatty acid ester having C 8 -C 20 chains or a mixture of alkoxylated polyhydric alcohols.
• the alkoxylate may be an ethoxylate and the degree of ethoxylation is between 20 and 500.
• the polyhydric alcohols may further comprise between 2 to 8 carbon atoms.
• the present invention relates to the aqueous cosmetic surfactant composition described above wherein the polymer is a C 8 -C 20 -fatty acid ester of alkoxylated C 8 -C 20 -fatty alcohols.
• the polymer of the aqueous cosmetic surfactant composition described above is a fatty acid diester or fatty alcohol diether of a polyglycol ether having an average molar weight of between 2,000 and 25,000.
• the present invention relates to aqueous cosmetic surfactant compositions of elevated viscosity containing 4 to 30% by weight of base surfactants, and 3 to 29.5% by weight of a thickener mixture and additive.
• the compositions are characterized in that the thickener mixture contains 3 to 25% by weight of alkyl polyglycoside, 0.005 to 2% by weight of a polymer and 0 to 2.5% by weight of a foreign electrolyte based on the aqueous, cosmetic surfactant composition.
• the recommended thickener mixture is as follows: 3 to 25% by weight of an alkyl polyglycoside, 0.005 to 2% by weight of a polymer, preferably 0.01 to 1.5%, and 0 to 2.5%, preferably 0 to 2% by weight, of a foreign electrolyte.
• Base surfactants are surfactants customary in aqueous cosmetic compositions, such as, in particular, fatty alcohol ether-sulphates, fatty alcohol sulphates, carboxymethylated fatty alcohol oxethylates, sulphosuccinates, alkane sulphonates, fatty acid salts, betaines, ampholytic compounds, fatty alcohol oxethylates, sorbitane esters, ethoxylated sorbitane esters, sugar esters or a mixture thereof.
• alkyl polyglycosides according to the present invention satisfy the formula I:
• R represents an alkyl radical having 8 to 18, preferably 10 to 18 carbon atoms, or a mixture thereof
• the alkyl radical may be straight-chained or branched, and either saturated or unsaturated.
• Alkyl polyglycosides having an HLB value between 11.5 and 17, which can be determined, for example, via the emulsion method are particularly preferred.
• the alkyl polyglycosides used according to the present invention can be prepared by known processes on the basis of raw materials which undergo secondary expansion. For example, dextrose is reacted in the presence of an acid catalyst with n-butanol to form butyl polyglycoside mixtures. These mixtures are subjected to transglycosidation with long-chain alcohols in the presence of an acid catalyst to give the desired alkyl polyglycoside mixtures.
• the structure of the product can be varied within certain limits.
• the alkyl radical R is determined by the choice of the long-chain alcohol.
• the most economical surfactant alcohols have between 10 to 18 C atoms, in particular, those having naturally occurring fatty alcohols from the hydrogenation of fatty acids or fatty acid derivatives are preferred, which are also available industrially. Ziegler alcohol or oxo alcohols may also be used.
• the polyglycosyl radical Z n is determined either by the choice of the carbohydrate or by the adjustment of the average degree of polymerization n, for example, in accordance with German Offenlegungsschrift (German Published Specification) 1,943,689.
• polysaccharides for example, starch, maltodextrines, dextrose, galactose, mannose, or xylose, for example, may be used.
• the industrially available carbohydrates, starch, maltodextrines and especially dextrose are preferred.
• the alkyl polyglycosides are always mixtures of oligomers, which in turn, are mixtures of various isomeric forms. They are present alongside one another with ⁇ - and ⁇ -glycoside bonds in pyranose and furanose form. The points of linkage between the two saccharide radicals also differ.
• Alkyl polyglycosides used according to the present invention may also be prepared by admixing alkyl polyglycosides with alkyl monoglycosides.
• the latter can be isolated or concentrated from alkyl polyglycosides, for example, in accordance with EP-A-0,092,355 using polar solvents, such as acetone.
• the degree of glycosidation is appropriately determined by means of 1 H-NMR.
• the alkyl polyglycosides are regarded as extremely environmentally friendly when compared with all other surfactants used in cosmetic cleansing agents.
• the degree of biological degradation of the alkyl polyglycosides according to the present invention is very high, measuring 96 ⁇ 3% when analyzed with a water treatment plant simulation 11/DOC model. This figure is measured against a background that regards as readily degradable a substance that has a 70% degree of degradation.
• the acute oral toxicity LD 50 (rat) and the aquatic toxicity (LC 50 (golden orfe) and EC 50 (Daphnia), at values of >10,000 mg/kg, 12 mg/1 and 30 mg/1 respectively, are more favorable by a factor of 3 to 5 than the corresponding values of the current most important surfactants.
• Polymers according to the present invention are, in particular, derivatives of alkoxylated, and in particular, ethoxylated, polyhydric alcohols having 2 to 8 C atoms, such as ethylene glycol, propanediol, glycerol, butandiol, erythritol, pentaerythritol, arabitol, or sorbitol, for example.
• Preferred derivatives are fatty acid esters and fatty alcohol ethers, the saturated or unsaturated, straight-chain or branched alkyl radicals being able to possess 8 to 20 carbon atoms and the average degree of alkoxylation being 20 to 500 mol/mol.
• R' is a straight-chain (or optionally branched), saturated or unsaturated, alkyl radical having 8 to 20 carbon atoms, or a mixture thereof
• R" is a straight-chain (or optionally branched) saturated or unsaturated, alkyl radical having 8 to 20 carbon atoms, or a mixture thereof
• m is an average number from 20 to 100.
• the fatty acid esters and/or fatty alcohol ethers of the polyglycol ethers having average molar masses between 2,000 and 25,000 are the preferred polymers.
• the alcohol end groups of the polyglycol ethers must substantially completely esterified or etherified.
• Polymers based on cellulose or xanthan are also suitable polymers but they are less preferred. Polymer mixtures can also be used.
• the surfactants customarily regarded as base surfactants in aqueous cosmetic compositions of the present invention are, in particular, fatty alcohol ether-sulphates, fatty alcohol sulphates, carboxymethylated fatty alcohol oxethylates, fatty alcohol ether-sulphosuccinates, alkane sulphonates, fatty acid salts, alkyl betaines, ampholytic compounds, fatty alcohol oxethylates, fatty acid sorbitane esters, ethoxylated sorbitane esters, sugar esters, and a mixture thereof, the chain length of the saturated or unsaturated, straight-chain or branched alkyl chain being in each case 8 to 22, preferably 10 to 20, carbon atoms, and the cations of the anionic surfactants are Na, K, NH 4 , C 2 -C 3 -alkanolammonium or Mg.
• the degrees of ethoxylation are between 1 and 5 (preferably between 2 and 4) mol of ethylene oxide/mol in the case of the fatty alcohol ether-sulphates, between 2 and 15 (3 to 10) ml of ethylene oxide/mol in the case of the carboxylated oxethylates, between 1 and 6 (2 to 4) mol of ethylene oxide/mol in the case of the fatty alcohol ether-sulphosuccinates and between 2 and 25 (2-15) mol of ethylene oxide/mol in the case of the fatty alcohol oxethylates.
• the viscosity of the aqueous surfactant compositions for cosmetic compositions according to the present invention may, if appropriate, be optimized by the addition of water-soluble electrolytes. Thus, the addition of these substances is advisable. Electrolytes which may be used for this purpose are, inter alia, alkali metal halides, sulphates or phosphates, ammonium halides, sulphate or phosphates, and alkaline earth metal halides, sulphates or phosphates.
• aqueous compositions according to the present invention may contain further components which are of importance for the particular application. Suitable components are, for example, silicone surfactants, hydrolyzed proteins, scents, turbidity and opalescent agents, fat restorers, silicone oils, humectants, preservatives, skin-cosmetic active compounds, plant extracts, buffers and complexing agents.
• Suitable components are, for example, silicone surfactants, hydrolyzed proteins, scents, turbidity and opalescent agents, fat restorers, silicone oils, humectants, preservatives, skin-cosmetic active compounds, plant extracts, buffers and complexing agents.
• Example 1 10 g of carboxymethylated C 12 -C 14 -fatty alcohol oxethylate (degree of carboxymethylation 95%) and 0.4 g of Antil® 141 solid were dissolved in water, and NaCl was added to the solution, as in Example 1.
• Sorbitol was ethoxylated (about 300 mol of EO/mol) at about 170° C. in the presence of NaOH and then esterified with stearic acid at about 210° C. and 30 mbar in the presence of isopropyl titanate as catalyst. The reaction is complete after about 8 h and the establishment of a OH number of ⁇ 5 mg KOH/g.
• the product, sorbital 300 EO hexastearate, has a softening point of about 60°C.
• the polymer prepared in this way is added in various concentrations to aqueous solutions of various mixtures of C 12 -C 14 -fatty alcohol ether-sulphate containing 2 mol of EO/mol and C 12 -C 14 -alkyl polyglycoside (degree of glycosidation 1.5, HLB value 13,8) in the presence of 1% NaCl.
• compositions according to the present invention display outstanding foaming power (Wilmsmann friction foam, 2 g/l) in the presence or absence of artificial sebum (30% triolein, 20% tristearin, 20% squalane, 15% oleic acid, 10% palmitic acid, 5% stearic acid) in comparison with commercially available shampoos.
• sorbitol polymer from Example 3 0.4 g was added to 7.5 g of C 12 -C 14 -fatty alcohol ether-sulphate containing 2 mol of (EO/mol and 7.5 g of C 12 -C 14 -alkyl polyglycoside having a degree of glycosidation of 1.5 (HLB value 13.8) and the solution was made up to 100 ml with water.
• the viscosity of the clear solution, measured at a shear rate of about 10 sec -1 was about 5,000 mPa.s.
• composition according to the present invention thickening appropriate for a shampoo can be achieved even with very low polymer concentrations without a foreign electrolyte.
• LIPOXOL® 4,000 polyethylene glycol, average molar mass 4,000
• 73.7 g of oleic acid and 0.6 g of isopropyl titanate were heated at 180° C. under a water pump vacuum for about 20 h until an acid number of ⁇ 1 mg KOH/g was obtained.
• 1% of Antil® solid was added to an aqueous solution containing 5% of C 12 -C 14 -fatty alcohol ethoxylate-sulphosuccinate and about 3 mol of EO/mol, 5% of C 12 -C 14 -alkyl polyglycoside (degree of glycosidation 1.3) and 1% of NaCl.
• the viscosity of the resulting clear gel is 17,000 mPa.s, measured at a shear rate of about 10 sec -1 .
• sorbitol polymer (compare Example 3) is added to an aqueous solution containing 5% of C 12 -C 14 -fatty alcohol ether-sulphate (2 mol of EO/mol), 5% of C 10 -C 12 -alkyl polyglycoside (HLB value 14.5) and 1% of NaCl.
• the viscosity of the solution is about 4,500 mPa.s, the clear point is 2° C. and the foaming power is outstanding.
• the resulting gel has a viscosity of about 15,000 mPa.s at a shear rate of 10 sec -1 and a clear point of 5° C.

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Citations (8)

• 1991
  • 1991-04-30 DE DE4114141A patent/DE4114141A1/de not_active Ceased
• 1992
  • 1992-02-22 AT AT92103006T patent/ATE125695T1/de active
  • 1992-02-22 EP EP92103006A patent/EP0511466B1/de not_active Revoked
  • 1992-02-22 DE DE59203074T patent/DE59203074D1/de not_active Revoked
  • 1992-02-22 ES ES92103006T patent/ES2077892T3/es not_active Expired - Lifetime
  • 1992-02-22 DK DK92103006.0T patent/DK0511466T3/da active
  • 1992-04-28 CA CA002067449A patent/CA2067449A1/en not_active Abandoned
  • 1992-04-28 NO NO92921653A patent/NO921653L/no unknown
  • 1992-04-28 JP JP4110469A patent/JPH05132411A/ja active Pending
• 1994
  • 1994-08-22 US US08/293,602 patent/US5464874A/en not_active Expired - Fee Related
• 1995
  • 1995-08-08 GR GR950402170T patent/GR3017047T3/el unknown

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